Choose from 3,267 vacation rentals located in Wailea, Hawaii. Top filters in Wailea include Internet / Wifi, Kitchen / Kitchenette, and Pool. Prices range from $85 to $10,185 per night. Our most popular vacation rental types near Wailea are Condo and Hotel.

Top vacation rentals in Wailea

Dining
5.0
Outstanding(209 Reviews)
Condo
 in Kihei
5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
2 guests · 1 bedroom · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Wailea at 5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View! for $195 for your next trip.

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Beach nearby, sun loungers, beach towels
4.9
Outstanding(251 Reviews)
Condo
 in Kihei
Absolutely Incredible Penthouse Front Facing Ocean Views with Pickleball!
2 guests · 1 bath
Pool · Kitchen / Kitchenette · Air conditioner

Condo in Wailea, for $199 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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Property view
4.3
Excellent(38 Reviews)
Resort
 in Wailea
Wailea Grand Champions Villas - CoralTree Residence Collection
Garden · Pool · Kitchen / Kitchenette

This attractive Resort in Wailea, $372 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Property view
4.5
Excellent(32 Reviews)
Resort
 in Wailea
Wailea Elua Village - CoralTree Residence Collection
Pool · Kitchen / Kitchenette · Air conditioner

When traveling to Wailea, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $385 per night.

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Vacation rentals with internet & wifi in Wailea

Dining
4.8
Outstanding(216 Reviews)
Condo
 in Kihei
Live Large. Experience the ultimate Maui.
3 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

Looking for a Condo in Wailea, this Condo for $249 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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Property view
4.7
Outstanding(110 Reviews)
Hotel
 in Wailea
5star
Hotel Wailea, Relais & Châteaux - Adults Only
Garden · Pool · Kitchen / Kitchenette

This Hotel for $372 in Wailea, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Beachfront
Property view
3.9
Good(561 Reviews)
Hotel
 in Wailea
2star
Days Inn by Wyndham Maui Oceanfront
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This attractive Hotel in Wailea, $282 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Beachfront
Property view
4.3
Excellent(191 Reviews)
Resort
 in Wailea
Fairmont Kea Lani, Maui
Garden · Pool · Kitchen / Kitchenette

Resort in Wailea, for $485 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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Wailea

Wailea travel guide

Let us help you plan your perfect Wailea vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Wailea, and more.

Frequently asked questions

What is the price range for rentals in Wailea?

Vacation rentals in Wailea have a price range between $85-$10,185. The average price for rentals in Wailea is $328 per night.

What are the most popular vacation rental amenities in Wailea?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Pool

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